Oak Street Tours and Activities

Oak Street

Plan a trip to see Oak Street

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was AU$6,062, price is now AU$5,097 per person
AU$5,097
per person
18 June - 25 June
just found
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,090 reviews)
I didn’t take advantage of breakfast

Reviewed on 9 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$6,811, price is now AU$5,560 per person
AU$5,560
per person
18 June - 25 June
just found
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$7,621, price is now AU$6,416 per person
AU$6,416
per person
18 June - 25 June
just found
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.

Reviewed on 14 Apr 2026

Tours & day trips

See all 198 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour
9.6 out of 10 with 1508 reviews
Free cancellation available
Price is AU$55 per adult
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Private & custom tours

See all 51 activities
Chicago: Creative Team Building - Paint Your Own Fluid Bear

Chicago: Creative Team Building - Paint Your Own Fluid Bear

10.0 out of 10 with 1 review
Free cancellation available
Price is AU$125 per adult
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Food, drink & nightlife

See all 30 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Activity duration is 2 hours and 30 minutes
8.0 out of 10 with 41 reviews
Price is AU$192 per adult
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Attractions

See all 20 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.8 out of 10 with 705 reviews
Free cancellation available
Price is AU$42 per adult
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Classes & workshops

See all 13 activities
Chicago Perfume Making Classes on Magnificent Mile

Chicago Perfume Making Classes on Magnificent Mile

Activity duration is 1 hour and 15 minutes
9.4 out of 10 with 10 reviews
Free cancellation available
Price is AU$119 per adult
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Popular places to visit

900 North Michigan Shops

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

900 North Michigan Shops
875 North Michigan Avenue

875 North Michigan Avenue

4.5/5(36 reviews)

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

875 North Michigan Avenue
Chicago Gold Coast highrise residential towers with a lakeshore beach in the foreground.

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Oak Street Beach
Water Tower view on Michigan Ave in Chicago City

Chicago Water Tower

4.5/5(19 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Chicago Water Tower
Water Tower Place

Water Tower Place

4.5/5(16 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
Holy Name Cathedral

Holy Name Cathedral

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Holy Name Cathedral

Top Oak Street Hotel & Accommodation Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Embassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Hotel Riu Plaza Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
20 E Chestnut St Chicago IL
Sofitel Chicago Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The Chicago Hotel Collection Ambassador Gold Coast
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Aloft Chicago Mag Mile
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Hotel Felix River North/Magnificent Mile
See all 4,176 properties in Oak Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.